


Riding The T

by DRHPaints



Category: Boston Teens: Cumberland Farms, Conan O'Brien - Fandom, Conan O'Brien RPF, Saturday Night Live, Saturday Night Live Sketches
Genre: Blow Jobs, Explicit Language, Explicit Sexual Content, F/M, Face-Fucking, Grinding, One Shot, Plot What Plot/Porn Without Plot, Semi-Public Sex, Smut, Spanking, Stranger Sex, Subways, Vaginal Fingering, Vaginal Sex, alcohol use, slut kink
Language: English
Status: Completed
Published: 2021-02-24
Updated: 2021-02-24
Packaged: 2021-03-14 21:02:17
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,461
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29673228
Author URL: https://archiveofourown.org/users/DRHPaints/pseuds/DRHPaints
Summary: Leila meets the handsome and direct Eric Pearson while riding the T back to Boston and the two get carried away in the compartment before he invites her back to his house for some fun.
Relationships: Conan O'Brien/Original Female Character(s), Eric Pearson/Original Female Character
Kudos: 3





	Riding The T

**Author's Note:**

  * For [damn_conan](https://archiveofourown.org/users/damn_conan/gifts).



> This is a fic based on Conan O'Brien's character, Eric Pearson, as portrayed when he hosted SNL in 2001 (Season 26 Ep. 14) Here's the link for those who haven't seen it and are curious:
> 
> https://youtu.be/yfqHHFIWzKE

Pressurized doors closing behind, Leila wove through the knot of bodies with downcast eyes and a polite smile until she could claim a space, grabbing the bar overhead in preparation for the journey to Boston. 

Passing the second stop with the elbow of a surly gentleman poking uncomfortably into her ribs, Leila felt strangely watched and turned around.

Sculpted jaw rolling as he chewed his gum, a man with stunningly pretty sky blue eyes checked her out from his immensely high perspective, large hand gripping the bar and casually resting his weight on one slender hip.

Catching her gaze, he tipped up his sharp chin and leaned his svelte frame forward. “So, uh...how’s it goin’?”

The guy sported perhaps the heaviest Southie accent Leila heard in some time and she couldn’t help but flash a blood red smile, looking up through her eyelashes. “Oh, I’m alright, I guess. How are you?”

“Good, good…” Continuing to scan her from head to toe, his tongue unconsciously darted over his thin lips, preening beneath his olive green jacket. “So what’s your name, beautiful?”

Usually Leila didn’t like someone so forward, but after a few drinks at her friend’s, not to mention an extensive cold streak in her love life, the affections of this tall, handsome stranger were more than welcome. “Leila…” Suppressing a giggle, she peeked from the corner of her green eyes, admiring his plethora of freckles. “You?”

“Eric. Eric Pearson.” Closing the gap between them with half a step, Eric positively loomed over Leila, his clean yet masculine scent intoxicating and paired with the mintiness of his gum. “So…” Eric took in the sight of Leila’s book bag and raised a faint ginger brow. “You go to Harvard, then?”

“Yeah…” Leila teetered her head and lifted a shoulder. She didn’t like to brag about her schooling. Many guys found the mere name of an Ivy League intimidating, so she skirted the issue as long as possible. “It’s not a big deal…”

Waving a big hand, Eric’s thin lower lip protruded, impressed. “Nah, that’s awesome. I knew you were wicked smart.” Eric broke out in a beaming smile and Leila unraveled, though how he came to this conclusion when his gaze lingered on Leila’s ample cleavage is anyone’s guess.

“Oh, thank you.” Leila nodded. Doing what she could to swivel in Eric’s direction given their cramped quarters, she grinned. “So, are you a student, too?”

Cerulean eyes sliding away, Eric hesitated for a second. “Oh nah, was just at a party in Mather House with my buddies. Actually I’m in the Coast Guard.” Eric didn’t think it pertinent to mention his AWOL status to this delicious dish on the train. 

“Oh wow, that’s…” Leila couldn’t help but picture his long body clothed in the uniform, mouth filling with saliva as she moved closer. “That’s pretty sexy…”

“Oh you think so, huh?” Taking a risk, Eric traced the line of Leila’s face with one lengthy finger, thin lip bitten.

Nodding, Leila couldn’t help but mold herself to his elongated frame, a little tipsy and feeling adventurous. “Definitely…”

Eric dipped down, tip of his nose etching over Leila’s face as his sizable hand squeezed her waist with a desirous hum. “Mmm...Leila…” Capturing her lips, a vague corner of Leila’s brain told her to stop, that she shouldn’t be making out on the T with a perfect stranger.

But Eric’s tongue twisting with her own, tasting of hops, peppermint, and novel excitement; and his touch, insistent and commanding as he hauled her hips forward, overran any reason, and Leila gave in. 

Fingers working into his short orange hair, Leila purred against Eric, unsure exactly when his big palm started kneading her ass as their heads tilted to deepen the kiss. “Mmm...fuck, you’re so sexy, Leila…” Reedy voice syrupy and deep, Eric’s knees bent and Leila sensed the beginnings of his erection through his light wash jeans.

Emerald eyes flashing open, Leila slyly perused the compartment surrounding them as Eric licked into her mouth. Thankfully many of the other patrons departed by now, and when Eric’s large hand ghosted over her breast above the shirt, none took notice. 

“Hey…” Eric murmured into the pale flesh of Leila’s neck before nipping at her ear. “You wanna come back to my house? Just a few more stops.”

“Yeah…” Nodding eagerly, Leila cautiously palmed Eric’s burgeoning erection, the discovery of his thick cock leaving her tingling in anticipation. “Yeah, I do.”

Chuckling wickedly, Eric’s strong grip closed around her wrist and he tipped Leila’s chin up to meet his piercing azure eyes. “Ah I see. You’re a bad girl, huh?”

Leila smirked and lifted a shoulder. “I could be…”

“Oh yeah?” 

With lightning speed, Eric spun her around, snatching Leila by the elbows and shoving her forward until her breasts smushed against the windows. “You like it like this, bad girl? Huh?”

Leila gasped and Eric’s fingers released. “Sorry, just playin’...if you’re not into it…” Scratching the back of his head, Eric took half a step away. “Sorry, I didn’t mean to scare you or anything.”

“No, no, it’s…” Beckoning for him to return, Leila cleared her throat. “It’s cool. Just caught me off guard. I’m up for it.”

“Fuckin’ sweet.” With a cursory glance over his shoulder. Eric didn’t really give a shit who watched. Grinding his turgid erection into the crack of Leila’s round ass with a groan, Eric roughly massaged her breasts and turned her face up to link their lips. “Mmm…”

Within minutes Leila arched her spine as Eric huffed into her mouth, thrusting her against the glass with squeaking abandon as a spot of precum dotted his jeans. Clit throbbing and unbelievably slick, only Leila’s last modicum of propriety prevented her from snagging Eric’s huge hand and sliding his fingers up her thigh. 

“Where--are we almost at your stop?” Leila breathed, fisting in Eric’s tangerine tresses as he breached her bra and rubbed a nipple to alertness. 

“Fuck!” Popping his head up, Eric looked around in alarm. “Shit! Yeah, let’s...it’s right here. Let’s go, babe.”

A lanky arm dragged Leila into the brisk Boston evening as soon as the automatic door opened. Laughing and trying to keep up with his long-legged strides, Eric rounded the corner to his modest home, smiling and breathless. “Here we are, babe. She’s not much, but this is my place.” 

Leila followed Eric inside, apprehensive when she joined her heels to several other pairs of shoes in the entryway. “Oh shit!” An elderly woman in a nightgown floated by and Leila clutched her chest. “Sorry…” Lowering her voice, she faced Eric. “Is that...your mom, or…?”

“Oh yeah, but don’t worry…” Continuing at full volume as he removed his boots, Eric waved a hand dismissively. “She’s deaf. We’re good. And my dad works nights.” Eric patted Leila’s ass and made his ginger eyebrows dance. “So don’t hold back, baby. We might as well be all alone.”

“Okay…” Looking after Eric’s mother nervously, she truly didn’t seem to clock their entrance or noises, so Leila did her best to relax as Eric led her back to his bedroom. 

Walls splashed with Red Sox posters and pennants, the Nomar Garciaparra on Eric’s t-shirt being the most prominent reflected player, he closed the door and approached Leila with a grin. “Mmm damn, am I glad I got on the T with you today, honey.”

Dropping her bag, Leila bobbed her head and draped her arms over Eric’s shoulders, smiling. “Me too.”

Eric shed his green jacket as he fused to Leila’s mouth, walking her backward to the bed with a mischievous chuckle. “Mmm...tell me you wanna get fucked hard, baby.”

“Yes, fuck…” Leila gasped as she tugged at his Red Sox shirt. “Anything. Please, just fuck me, Eric.”

Smirking, Eric threaded through Leila crimson mane as his other hand went to his belt. “Oh yeah? You want my cock, don’t you? Are you gonna be a good little slut for me? Huh, Leila?”

Eric’s slightly nasal voice intoning the words as his crystalline blue eyes drilled mercilessly trapped Leila’s breath in her lungs and she nodded enthusiastically. “Yeah. Yeah, I am.”

“Good.” Eric sneered, placing a big hand atop her head and guiding Leila down until she dropped to her knees. “Then fuckin’ suck me. Now.”

Helping him shrug the denim down his skinny thighs, Leila’s green eyes widened at the massive curve as Eric unearthed his cock from his (to no surprise) Red Sox boxers. Leila encased his shaft with her fingers, appreciating every vein and ridge as her lips neared the wide, artfully carved head before she took Eric into her mouth.

“Mmm...fuck yeah…” Eric rolled his narrow hips forward, plunging his thick cock into the restrictive heat of Leila’s throat. Tongue firm against the underside and hollowing her cheeks, Leila’s eyes watered when Eric’s tip prodded, but she persisted, breathing through her nose as his pelvis rocked and he groaned above. “ _ Fuck! Yeah, suck me, Leila! Your mouth...so fuckin’ good!” _

Big hands fisting in her scarlet tresses, Eric’s tall stature splintered with a wheeze as he smacked into the wet circle of Leila’s lips, cradling her skull close. “ _ Oh fuck! Baby, you suck me so good! Fuck yeah! I love your mouth! Fuck, Leila! Keep going! Suck me, baby! Go deep! Fuck! Fuck! Yeah!” _

Fondling his balls with the other hand looped around his narrow waist, Leila allowed the saliva to pool in the corners of her mouth, strings of drool wobbling to the floor as the velocity of Eric’s strokes increased. “ _ Fuck! Fuck, baby! Yeah! So damn good! Fuck! Fuck! Fuck!” _

With a sound somewhere between a moan and a snarl, Eric stuttered to a stop, yanking on Leila’s red locks and shaking his head. “Nah…” Chest heaving, Eric blinked and tapped her shoulder, puffing out his cheeks. “I still gotta fuck you, baby. C’mon.”

Smearing the back of her hand across her face, Leila nodded and Eric helped her up. “So…” Rapidly peeling her shirt overhead, Eric swept in to steal hungry kisses as he stripped Leila of her clothing. “You want me to pound that pussy, huh?” Eric whipped Leila around and expertly unclasped her bra, breath hot and ticklish against her ear as he exposed her breasts with a grin. “Don’t fuckin’ lie to me, slut. I know exactly what you want…”

Even if Leila were tempted to deceive him, once Eric unzipped her skirt, long fingers sneaking past the waistband of her panties to pet over the lips of her pussy as he pinned her back to his chest, she couldn’t think clearly enough to say anything besides, “ _ Yes! Fuck! Please! Yes!” _

“Thought so…” With an impish chuckle, Eric tossed her onto the bed, ripping Leila’s panties down and flinging the scrap of fabric away. “Just you wait, Leila.” Eric disrobed, revealing his lightly muscled abdomen adorned with orange hair and long dancer’s legs, all exceptionally pale and speckled. Curling Leila back by a handful of auburn tendrils as he tore open a condom with his teeth, Eric smiled. “Good fuckin’ luck gettin’ through Harvard, baby. Because I’m gonna fuck your brains out.”

Eric kneaded Leila’s plump ass, slivered lips touching a kiss to her neck. “You ready, hun?”

“Yes.” Leila wiggled her knees apart a bit further atop the mattress, bracing her palms. “Fuck me.”

“Mmm…” Rolling forward into the moist warmth, Eric’s sea blue eyes fluttered closed and his crisp jaw dropped. “Fuck...you feel so damn good…” Eric hooked a large hand around to thrum Leila’s clit as he rotated leisurely, rejoicing in every slippery surface of her drenching pussy. “Fuck yeah...I’m gonna make you cum so hard on my cock, Leila.”

“Fuck.  _ Yes!”  _ Rocking back onto Eric’s thick cock and moaning, pulses of pleasure radiated from between Leila’s legs outward and the pitch of her ecstasy rose. “ _ Harder! Fuck!” _

Eric brought a sizable palm cracking down over Leila’s asscheek with a boundless grin and propelled his hips forward vigorously. “Like this, huh? Like this? Is this how you want it, you fuckin’ slut?”

As Eric clapped into her, ruthlessly hammering Leila’s g-spot until her emerald eyes twitched and she scrambled over the sheets, she started to scream. “ _ Fuck! Fuck, yes! Eric! Don’t stop! Fuck! Fuck! Eric!” _

Freckled fingers racing over her clit, Eric nodded in approval as Leila’s sopping pussy constricted. “ _ Fuck yeah, baby! Cum on my cock! I know you love it! Say it! Say you love my cock! C’mon, you slut! Say it! Scream for me, baby!” _

_ “I love it, fuck! Fuck! I love your cock, Eric! Yes! Yes!” _ Collapsing to her elbows in her convulsions, Leila’s breath condensed in the sheets, flinching around Eric’s plowing erection. “ _ Fuck! Fuck…” _

Eric spanked Leila again and again until a perfect pink imprint of his huge hand remained on her voluptuous ass. “ _ Mmm...fuck yeah!”  _ Scooping Leila up, Eric laid her flat, kneeing her legs apart a tad before weighing her down on the bed with his long body. 

Leila purred delightedly as one of Eric’s wiry arms crossed her chest, the other jamming between her and the mattress to spin over her clit. “Mmm...Leila…”

Eric arched into the pulsating warmth, urging Leila’s mouth back for sloppy, urgent kisses as whimpers overcame his pale, sweating form. “ _ Oh fuck! Baby, you’re gonna make me cum so hard! Fuck, Leila! Yeah, baby! I love fuckin’ your pussy so damn much! Gonna cum! Fuck! Fuck!”  _

Bumping back against Eric and shrieking, Leila cinched around him again, squeezing Eric’s carved forearm as her eyes rolled. “ _ Eric! Fuck! I’m cumming! Yes! Fuck! Fuck!” _

_ “Fuck!”  _ The intense pressure scrunching his chiseled features and flexing every muscle in his tall frame, Eric froze atop Leila in silence. With a roiling grunt his pelvis stammered, nailing her down to the bed repeatedly before he fell boneless above.

Leila continued to throb around Eric’s softening cock as he lifted a lazy speckled hand to smooth the strands of red from her dewy face. “Mmm...that was wicked awesome.”

“Hell yeah it was.” Gulping air, Leila nodded against the sheets and claimed Eric’s mouth for a languid kiss before he rolled away to dispose of the condom.

Eric returned to find Leila recovering at the top of the bed and offered a Mighty Ale. “Sorry, I only have one left. But it’s all yours, babe.”

“Aw, that’s alright.” Popping the can open, Leila sipped and passed the beer back to Eric with a smile. “We can share.”

“Yeah.” Taking a swig, Eric lassoed Leila near with a lanky arm, planting a kiss to her temple as they nestled naked atop his Red Sox sheets. “What’d I say? Knew you were smart.” 

**Author's Note:**

> Thank you for taking the time to read! If you enjoyed this story, please leave a comment or come say hi on tumblr at fandomtransmandom. I also accept requests!


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